NO146983B - APPLICATION OF ALFA-ACYLOXY-N, N - Google Patents

APPLICATION OF ALFA-ACYLOXY-N, N Download PDF

Info

Publication number
NO146983B
NO146983B NO773006A NO773006A NO146983B NO 146983 B NO146983 B NO 146983B NO 773006 A NO773006 A NO 773006A NO 773006 A NO773006 A NO 773006A NO 146983 B NO146983 B NO 146983B
Authority
NO
Norway
Prior art keywords
carbon atoms
activators
acyloxy
compounds
radicals
Prior art date
Application number
NO773006A
Other languages
Norwegian (no)
Other versions
NO773006L (en
NO146983C (en
Inventor
Jean-Pierre Schirmann
Bernard Dubreux
Michel Bakes
Serge-Yvon Delavarenne
Marie-Christine Daude-Lagrave
Original Assignee
Ugine Kuhlmann
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ugine Kuhlmann filed Critical Ugine Kuhlmann
Publication of NO773006L publication Critical patent/NO773006L/en
Publication of NO146983B publication Critical patent/NO146983B/en
Publication of NO146983C publication Critical patent/NO146983C/en

Links

Classifications

    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61KPREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00Cosmetics or similar toiletry preparations
    • A61K8/18Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/40Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing nitrogen
    • A61K8/42Amides
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00Preparations for care of the skin
    • A61Q19/02Preparations for care of the skin for chemically bleaching or whitening the skin
    • AHUMAN NECESSITIES
    • A61MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61QSPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q5/00Preparations for care of the hair
    • A61Q5/08Preparations for bleaching the hair
    • CCHEMISTRY; METALLURGY
    • C11ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11DDETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
    • C11D3/00Other compounding ingredients of detergent compositions covered in group C11D1/00
    • C11D3/39Organic or inorganic per-compounds
    • C11D3/3902Organic or inorganic per-compounds combined with specific additives
    • C11D3/3905Bleach activators or bleach catalysts
    • C11D3/3907Organic compounds
    • C11D3/3917Nitrogen-containing compounds

Description

Foreliggende oppfinnelse angår anvendelse av a-acyl-oksy-N,N'-polyacylmalonamider som aktivatorer for uorganiske og organiske perforbindelser, spesielt for hydrogenperoksyd, addisjonsprodukter derav med organiske stoffer slik som urea og dicykloheksylamin, samt disses uorganiske persalter slik som perborater, perkarbonater og perfosfater. The present invention relates to the use of α-acyl-oxy-N,N'-polyacylmalonamides as activators for inorganic and organic per compounds, especially for hydrogen peroxide, addition products thereof with organic substances such as urea and dicyclohexylamine, as well as their inorganic per salts such as perborates, percarbonates and perphosphates.

Virkningen av vandige oppløsninger av perforbindél—-ser som oksydasjonsmidler og blekemidler blir ikke effektiv før ved temperaturer over 70°C og fortrinnsvis mellom 80 og 100°C. The effect of aqueous solutions of perforbindels as oxidizing agents and bleaching agents does not become effective until temperatures above 70°C and preferably between 80 and 100°C.

Den kjente teknikk beskriver tallrike produkter som oppviser egenskaper som aktivatorer for perforbindelser, dvs. som tillater å oppnå en oksyderende virkning eller en blekevirkning hurtigere enn det man vanligvis ser, eller videre å utvikle denne virkning under temperaturbetingelser langt under det som er nødvendig i tilfelle deres fravær, og alle disse forbindelser er karakterisert ved at de har én eller flere per-hydrolyserbare funksjoner. The prior art describes numerous products which exhibit properties as activators for per compounds, i.e. which allow to obtain an oxidizing effect or a bleaching effect faster than is usually seen, or further to develop this effect under temperature conditions far below what is necessary in the case of their absence, and all these compounds are characterized by having one or more per-hydrolysable functions.

På området bleking er det kjent en rekke aktivator-forbindelser med kommersiell anvendelse. Litteraturen på dette område nevner spesielt poly-N-acetylerte heterocykler av typen hydantoiner, benzimidazoler og diketopiperaziner. Imidlertid har denne utvikling ikke fortsatt fordi stoffene oppviser alvorlige mangler idet de er ustabile overfor fuk-tighet og således hydrolyserer spontant, hvorved de hurtig minster sin aktivatoregenskap. Videre nødvendiggjør disse produkter spesielle forholdsregler med henblikk på lagring, behandling eller tilsetning til andre bestanddeler slik de f.eks. inngår i den vanlige sammensetning i et vaskepulver. Forskjellige løsninger er foreslått for å oppheve disse mangler: Innkapsling, separat kondisjonering, tilsetning av tørke-midler, men ingen av disse har vært tilfredsstillende, enten fordi de har gitt praktiske tekniske problemer eller fordi de har ført til en betydelig økning av prisen. In the area of bleaching, a number of activator compounds with commercial use are known. The literature in this area mentions in particular poly-N-acetylated heterocycles of the type hydantoins, benzimidazoles and diketopiperazines. However, this development has not continued because the substances show serious shortcomings in that they are unstable to moisture and thus hydrolyze spontaneously, whereby they quickly lose their activator properties. Furthermore, these products necessitate special precautions with a view to storage, treatment or addition to other components as they e.g. included in the usual composition of a washing powder. Various solutions have been proposed to overcome these shortcomings: encapsulation, separate conditioning, addition of drying agents, but none of these have been satisfactory, either because they have caused practical technical problems or because they have led to a significant increase in price.

Det foreligger således et industrielt behov for aktivatorer for perforbindelser, aktivatorer som er stabile under de vanlige betingelser for lagring og behandling. There is thus an industrial need for activators for per compounds, activators which are stable under the usual conditions for storage and processing.

Foreliggende oppfinnelse har til hensikt å løse de ovenfor angitte problemer og angår anvendelse av a-acyloksy-N,N<1->polyacylmalonamider med formelen: The present invention aims to solve the above-mentioned problems and concerns the use of α-acyloxy-N,N<1->polyacylmalonamides with the formula:

der R^, I^, R3, R 4/ R5 og Rg som er like eller forskjellige betyr hydrogen, lineære alkylrester med 1-11 karbonatomer, forgrenede alkyl- og cykloalkylrester med 3-12 karbonatomer, hydrokarbonrester med 6-12 karbonatomer, som omfatter minst én aromatisk kjerne, eller der R , R£, R-j og R^ er definert som ovenfor mens R,, og/eller R^ er en acylgruppe COR^, der R^ er hydrogen eller en lineær eller forgrenet alkylrest med 1-12 karbonatomer eller en hydrokarbonrest med 6-12 karbonatomer omfattende minst én aromatisk kjerne, hvilke rester eventuelt kan være substituert med én eller flere hydroksy-, klor-, brom-, fluor-, jod-, nitro-, alkoksy-, amino-, ester-, amid- og etergrupper, som aktivatorer for perforbindelser, særlig for hydrogenperoksyd og addisjonsforbindelser derav. where R^, I^, R3, R4/R5 and Rg which are the same or different mean hydrogen, linear alkyl radicals with 1-11 carbon atoms, branched alkyl and cycloalkyl radicals with 3-12 carbon atoms, hydrocarbon radicals with 6-12 carbon atoms, which comprises at least one aromatic nucleus, or where R, R£, R-j and R^ are defined as above while R,, and/or R^ is an acyl group COR^, where R^ is hydrogen or a linear or branched alkyl residue with 1- 12 carbon atoms or a hydrocarbon residue with 6-12 carbon atoms comprising at least one aromatic core, which residues may optionally be substituted with one or more hydroxy, chlorine, bromine, fluorine, iodine, nitro, alkoxy, amino, ester, amide and ether groups, as activators for per compounds, especially for hydrogen peroxide and addition compounds thereof.

Som illustrasjon kan a-acyloksy-N,N'-polyacylmalon-amidene av formel (I) være a-acetoksy-a-metyl-N,N'-di-acetylmalonamid, a-propionoksy-a-metyl-N,N'-dipropionylmalonamid og a-acetoksy-ot-mety 1-N, N '-dipropionylmalonamid. By way of illustration, the α-acyloxy-N,N'-polyacylmalonamides of formula (I) may be α-acetoxy-α-methyl-N,N'-di-acetylmalonamide, α-propionoxy-α-methyl-N,N' -dipropionylmalonamide and α-acetoxy-ot-methyl 1-N,N'-dipropionylmalonamide.

En spesielt fordelaktig måte for anvendelse av aktivatorene ifølge oppfinnelsen består i å tilsette disse til perforbindelsen i en mengde på ca. 0,33 mol pr. mol perforbindelse som skal aktiveres. Imidlertid kan man etter behov arbeide med et underskudd eller overskudd av aktivator og med molforhold mellom aktivator og perforbindelse som ligger mellom 0,1 og 10. A particularly advantageous way of using the activators according to the invention consists in adding these to the per compound in an amount of approx. 0.33 mol per mol per compound to be activated. However, if necessary, one can work with a deficit or excess of activator and with a molar ratio between activator and per-compound that is between 0.1 and 10.

Aktivatorene av formel (I) kan benyttes i The activators of formula (I) can be used in

alle tilfeller der en perforbindelse benyttes for å oppnå en oksyderende eller blekende virkning, f.eks. ved bleking av tekstilfibre, olje, fett og voks, behandling av hår eller hud på kosmetologisk måte, passivering av metalloverflater, rense-teknikker, desinfeksjon og sterilisering. all cases where a compound is used to achieve an oxidizing or bleaching effect, e.g. by bleaching textile fibres, oil, fat and wax, treating hair or skin in a cosmetological way, passivating metal surfaces, cleaning techniques, disinfection and sterilisation.

Aktivatorene av formel (I) som tilsettes til perforbindelser eller en sammensetning inneholdende én eller flere perforbindelser, f.eks. et vaskemiddel, tilsikter å oppnå en blekende eller oksyderende virkning adskillig hurtigere ved en gitt temperatur, de tillater likeledes på samme måte å oppnå den samme blekevirkning ved å arbeide ved lavere temperatur . The activators of formula (I) which are added to per compounds or a composition containing one or more per compounds, e.g. a detergent, aims to achieve a bleaching or oxidizing effect much faster at a given temperature, they likewise allow the same bleaching effect to be achieved by working at a lower temperature.

Ved nærvær av natriumperborat i et vaskemiljø tillater f.eks. aktivatorene ifølge oppfinnelsen ved temperaturer mellom 30 og 50°C å oppnå en blekevirkning som i det vesent-lige er ekvivalent den som oppnås ved aktivatorenes fravær ved høyere temperaturer i størrelsesorden 80°C. In the presence of sodium perborate in a washing environment allows e.g. the activators according to the invention at temperatures between 30 and 50°C to achieve a bleaching effect which is essentially equivalent to that achieved in the absence of the activators at higher temperatures of the order of 80°C.

De følgende eksempler skal illustrere oppfinnelsen. The following examples shall illustrate the invention.

Eksempel 1- 3 Example 1-3

I et rom i et "AHIBA" bad med en temperatur på 40°C ble det tilført 250 ml av en vandig o<p>pløsning inneholdende 5 g/l av et vaskemiddel med følgende sammensetning: In a room in an "AHIBA" bath with a temperature of 40°C, 250 ml of an aqueous solution containing 5 g/l of a detergent with the following composition was added:

samt 1,7 g/l natriumperborattetrahydrat. as well as 1.7 g/l sodium perborate tetrahydrate.

I et annet rom ble den samme oppløsning tilsatt, men aktivatoren som skulle prøves i en konsentrasjon på In another room, the same solution was added, but the activator to be tested at a concentration of

1 g/l. 1 g/l.

I hvert av rommene ble det anbragt et stykke bomullsvevnad "EMPA", impregnert med standardiserte vinflek-ker . In each of the rooms, a piece of cotton fabric "EMPA" was placed, impregnated with standardized wine stains.

Etter 15 minutters vasking ble vevnadene skylt under en strøm av kaldt vann og deretter tørket ved omgivelsestem-peraturer. Blekekraften defineres som forskjellen mellom hvithetsindeksen (målt ved hjelp av et "ELREPHO" spektrofoto-meter med filter nr. 6) før og etter vasking, angitt som prosent av et hvithetsmaksimum på 100. After 15 minutes of washing, the tissues were rinsed under a stream of cold water and then dried at ambient temperatures. The bleaching power is defined as the difference between the whiteness index (measured using an "ELREPHO" spectrophotometer with filter No. 6) before and after washing, expressed as a percentage of a whiteness maximum of 100.

Man oppnår følgende resultater: The following results are achieved:

Eksempel 4- 6 Example 4-6

Man arbeider under de samme betingelser som ovenfor, men med en vasketemperatur på 20°C i stedet for 4 0°C. You work under the same conditions as above, but with a washing temperature of 20°C instead of 40°C.

Claims (1)

Anvendelse av a-acyloksy-N,N'-polyacylmalonamiderUse of α-acyloxy-N,N'-polyacylmalonamides med formelenwith the formula der R-^, R2'<R>3, R4, R5 og Rg, som er like eller forskjellige ( betyr hydrogen, lineære alkylrester med 1-11 karbonatomer, forgrenede alkyl- og cykloalkylrester med 3-12 karbonatomer, hydrokarbonrester med 6-12 karbonatomer, som omfatter minst én' aromatisk kjerne, eller der R1, R2, R3 og R4 er definert som ovenfor mens R^ og /eller R^ er en acylgruppe COR^, der R7 er hydrogen eller en lineær eller forgrenet alkylrest med 1-12 karbonatomer eller en hydrokarbonrest med 6-12 karbonatomer omfattende minst én aromatisk kjerne, hvilke rester eventuelt kan være substituert med én eller flere hydroksy-, klor-, brom-, fluor-, jod-, nitro-, alkoksy-, amino-, ester-, amid- og etergrupper, som aktivatorer for perforbindelser, særlig for hydrogenperoksyd og addisjonsforbindelser derav.where R-^, R2'<R>3, R4, R5 and Rg, which are the same or different ( means hydrogen, linear alkyl radicals with 1-11 carbon atoms, branched alkyl and cycloalkyl radicals with 3-12 carbon atoms, hydrocarbon radicals with 6- 12 carbon atoms, comprising at least one' aromatic core, or where R1, R2, R3 and R4 are defined as above while R^ and/or R^ is an acyl group COR^, where R7 is hydrogen or a linear or branched alkyl residue with 1 -12 carbon atoms or a hydrocarbon residue with 6-12 carbon atoms comprising at least one aromatic core, which residues may optionally be substituted with one or more hydroxy, chlorine, bromine, fluorine, iodine, nitro, alkoxy, amino , ester, amide and ether groups, as activators for per compounds, especially for hydrogen peroxide and addition compounds thereof.
NO773006A 1976-09-01 1977-08-31 APPLICATION OF ALFA-ACYLOXY-N, N NO146983C (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7626325A FR2363629A1 (en) 1976-09-01 1976-09-01 ACTIVATORS FOR PERCOMPOSES

Publications (3)

Publication Number Publication Date
NO773006L NO773006L (en) 1978-03-02
NO146983B true NO146983B (en) 1982-10-04
NO146983C NO146983C (en) 1983-01-26

Family

ID=9177298

Family Applications (1)

Application Number Title Priority Date Filing Date
NO773006A NO146983C (en) 1976-09-01 1977-08-31 APPLICATION OF ALFA-ACYLOXY-N, N

Country Status (16)

Country Link
JP (1) JPS6031879B2 (en)
BE (1) BE858048A (en)
BR (1) BR7705823A (en)
CA (1) CA1088954A (en)
CH (1) CH626398A5 (en)
DE (1) DE2738976C3 (en)
DK (1) DK145829C (en)
ES (1) ES462018A1 (en)
FR (1) FR2363629A1 (en)
GB (1) GB1563635A (en)
IE (1) IE45372B1 (en)
IT (1) IT1083604B (en)
LU (1) LU78047A1 (en)
NL (1) NL7709591A (en)
NO (1) NO146983C (en)
SE (1) SE434960B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2831899A1 (en) * 1978-07-20 1980-02-07 Basf Ag USE OF ACYLATED PHOSPHORIC OR SULFURIC ACID AS A CLEAR BLEACH ACTIVATOR FOR DETERGENT-RELEASING COMPONENTS CONTAINING ACTIVE OXYGEN
US4199466A (en) * 1978-08-21 1980-04-22 Shell Oil Company Activated bleaching process and compositions therefor

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AR204021A1 (en) * 1973-12-04 1975-11-12 Hoechst Ag WASHING AND WHITENING OXIDIZING AGENTS CONTAINING INORGANIC PERCOMPOSES AND TEXTILE WHITENING PROCEDURE
JPS5313355B2 (en) * 1974-03-18 1978-05-09
FR2363541A1 (en) * 1976-09-01 1978-03-31 Ugine Kuhlmann ACYLOXY-N, N 'DIACYLMALONAMIDES AND THEIR METHOD OF PREPARATION

Also Published As

Publication number Publication date
FR2363629A1 (en) 1978-03-31
DK145829C (en) 1983-09-05
NL7709591A (en) 1978-03-03
DE2738976A1 (en) 1978-03-02
IE45372B1 (en) 1982-08-11
DK383677A (en) 1978-03-02
IT1083604B (en) 1985-05-21
FR2363629B1 (en) 1980-05-30
BE858048A (en) 1978-02-24
DK145829B (en) 1983-03-14
JPS5330485A (en) 1978-03-22
NO773006L (en) 1978-03-02
SE434960B (en) 1984-08-27
JPS6031879B2 (en) 1985-07-24
BR7705823A (en) 1978-06-27
GB1563635A (en) 1980-03-26
LU78047A1 (en) 1979-05-23
DE2738976C3 (en) 1980-02-07
ES462018A1 (en) 1978-12-16
SE7709694L (en) 1978-03-02
CA1088954A (en) 1980-11-04
DE2738976B2 (en) 1979-06-07
NO146983C (en) 1983-01-26
CH626398A5 (en) 1981-11-13
IE45372L (en) 1978-03-01

Similar Documents

Publication Publication Date Title
US4128494A (en) Activators for percompounds
US3986972A (en) Acyl nitrile compounds as peroxygen bleach activators
CA1061503A (en) Inhibiting dye transfer in washing or bleaching
US3969257A (en) Washing and bleaching composition containing bleach, activator and a nitrilotricarboxylic acid compound
GB1513305A (en) Bleaching compositions and method of bleaching
US3882035A (en) Iminodiacetonitrile derivatives as peroxygen bleach activators
US4235599A (en) Bleaching composition
JP2007302891A (en) Protective use
NO146670B (en) APPLICATION OF ALFA-ACYLOXY-N-ACYL AMIDES AS ACTIVATOR FOR PERFORMANCE
US3816324A (en) Bleaching compositions containing a n-acyl azole
US3655567A (en) Bleaching and detergent compositions
NO146983B (en) APPLICATION OF ALFA-ACYLOXY-N, N
US3912648A (en) Ring halogen-free substituted triazine compounds as bleach activators
US3886078A (en) N-benzoylsaccharin as peroxygen bleach activator
CA1118162A (en) Peroxygen bleaching and compositions therefor
US3525695A (en) Laundry washing process
US3986974A (en) Aroyl-n-hydroxyformimidoyl halides as bleach activators
CA1084256A (en) Phosphorylated potentiators for percompounds
US3986971A (en) 2,4-diisocyanato-6-halo-s-triazines as peroxygen bleach activators
US4120809A (en) Washing and bleaching with composition containing bleach activator and a nitrilotricarboxylic acid compound
US3986973A (en) Cyanoformates and cyanoformamides as bleach activators
US3824188A (en) Halogen-substituted azine compounds as peroxygen bleach activators
NO164115B (en) PROCEDURE FOR WHITING THE HOUSEHOLD WASH IN A WASHING CYCLE.
US3073666A (en) Alkyl phosphate activators for inorganic peroxide bleaching
JPH03140400A (en) Two-agent type liquid bleaching agent composition